diff --git a/app/tasks/extract_metadata_with_gpt.py b/app/tasks/extract_metadata_with_gpt.py
index f4c7163b..e673e3bf 100644
--- a/app/tasks/extract_metadata_with_gpt.py
+++ b/app/tasks/extract_metadata_with_gpt.py
@@ -129,16 +129,16 @@ def extract_metadata_with_gpt(self, filename: str, cleaned_text: str, file_id: i
         import re
         filename = metadata.get("filename", "")
         if filename:
-            # Check if filename contains only safe characters (alphanumeric, dash, underscore, period, space)
-            # This matches the sanitize_filename behavior but validates before use
-            if not re.match(r'^[\w\-\. ]+$', filename):
+            # Check if filename contains only safe characters AND explicitly check for ".."
+            # Defense in depth: While the regex [\w\-\. ]+ already excludes / and \,
+            # we explicitly reject ".." to guard against:
+            # 1. Potential locale-specific \w behavior
+            # 2. Files literally named ".." which are valid but problematic
+            # 3. Future code changes that might relax the regex
+            if not re.match(r'^[\w\-\. ]+$', filename) or ".." in filename:
                 logger.warning(f"[{task_id}] Invalid filename format from GPT: '{filename}', using fallback")
                 # Reset to empty to trigger fallback to original filename
                 metadata["filename"] = ""
-            # Additional check: ensure no path traversal patterns
-            elif ".." in filename or "/" in filename or "\\" in filename:
-                logger.warning(f"[{task_id}] Path traversal attempt in GPT filename: '{filename}', using fallback")
-                metadata["filename"] = ""
         
         logger.info(f"[{task_id}] Extracted metadata: {metadata}")
         log_task_progress(
diff --git a/tests/test_path_traversal_security.py b/tests/test_path_traversal_security.py
index 6c61951c..878b547d 100644
--- a/tests/test_path_traversal_security.py
+++ b/tests/test_path_traversal_security.py
@@ -220,7 +220,8 @@ class TestExtractMetadataFilenameValidation:
         """Test that invalid filename formats are rejected."""
         import re
         
-        # Valid pattern from sanitize_filename: alphanumeric, dash, underscore, period, space
+        # Valid pattern from extract_metadata_with_gpt.py
+        # TODO: Consider extracting this to a shared constant to avoid duplication
         valid_pattern = r'^[\w\-\. ]+$'
         
         # Test valid filenames
@@ -376,10 +377,10 @@ class TestFileUploadSecurity:
             # os.path.basename should extract just the filename
             basename = os.path.basename(malicious)
             
-            # Verify no path traversal remains
-            assert ".." not in basename or malicious.endswith("..")
-            assert "/" not in basename
-            assert "\\" not in basename
+            # Verify no path traversal remains in basename
+            assert ".." not in basename, f"Path traversal not removed: {malicious} -> {basename}"
+            assert "/" not in basename, f"Path separator not removed: {malicious} -> {basename}"
+            assert "\\" not in basename, f"Path separator not removed: {malicious} -> {basename}"
 
     def test_sanitize_after_basename(self):
         """Test that sanitization happens after basename extraction."""